42 Wholesomely Funny Family Photos That Prove Awkward Moments Make The Best Memories
Ah, family—life’s greatest blessing and sometimes its most unintentionally hilarious source of chaos. If you’ve ever posed for a holiday photo in matching sweaters or tried to look normal while your toddler was mid-meltdown, you already know: Wholesomely Funny Family Photos are practically a universal experience.
This delightful collection of 42 photos from the Awkward Family Photos Instagram account is here to deliver that rare combination of secondhand embarrassment and heartfelt joy. You’ll witness haircuts that defy gravity, poses that raise questions, and facial expressions only a mother could frame.
These pictures are like that one casserole at every family reunion—strange, comforting, and weirdly unforgettable. One scroll through this list and you’ll be laughing, cringing, and nodding in agreement like, “Yep, we’ve got one of those too.”
#1. “Me and my brother at the National Zoo. My mom claims she and my dad never noticed the elephants banging in the water in the background but I don’t buy it.”
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#2. My mom has this picture hanging on her wall in her house for everyone to see. She sends it to me every Mother’s Day. This is me when my kids were little. Apparently they needed me and so did the dog, while I was on the toilet.
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#3. “Our deaf cattle dog has no idea he farts all the time and here’s our daughter reacting to his latest burst of gas.”
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#4. My sisters and I were professionally photographed with identical dolls in matching prairie dresses.
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#5. “I received this photo from my Dad while he was babysitting my daughter. When she found out Grandpa could take out his teeth, he let her wear them.”
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#6. My dad and I getting ready for a road trip in the summer of ’86.
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#7. “My husband as an infant. I prayed our children would not inherit his large cranium.”
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#8. During our wedding vows, while my husband promised to love my kids as his own, my kids were whisper-screaming at each other the whole time.
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#9. This miraculous photo is of my darling dear mother, in the 80s, with what is obviously a cutout of the great Thomas Sullivan Magnum. The best part of this photo is the glasses, but, the second best part is the fact that my mom refuses to admit that it is a cutout.
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#10. “This picture was taken at my daughter’s preschool. I think the photographer thought having her hold a flower would make for a really cute and innocent picture.”
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#11. I told my dad I wanted to be an ear for Halloween. He really came through.
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#12. My mall glamour shots from 1997 where I look like a woman who just cashed her husband’s life insurance check.
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#13. “Our kids had experimented with a few different poses and by the time I got my camera figured out, our son had found a new perch.”
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#14. 2nd grade, 1985. Was I going to recess or into the typing pool?
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#15. “As a child, my boyfriend loved appliances and in his eyes, all other appliances paled in comparison to the vacuum cleaner. When he was around five, his mom took him to a photography studio to get his portrait taken. He asked the photographers if they had any vacuums he could take a picture with. They found one in a broom closet and brought it out for him… the rest is history.”
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#16. My two-year-old daughter drew a pillow with chalk, then laid down for a nap.
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#17. We didn’t have much money in 1977 but that didn’t stop Mom from giving us our wish to be C3P0 and R2-D2 that Halloween.”
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#18. “My mom had a very unique cure for my sunburn.”
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#19. This is how I found my husband and son after a diaper change. Neither was aware anything was amiss. It still makes me laugh 10 years later.
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#20. I came across this photo in a box in my parents’ garage, of my family and me. And no, it wasn’t Halloween.
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#21. The whole family seems to be so content as I choke off to the side and this is the epitome of my life. I am alive and well now – no thanks to any of my relatives :)”
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#22. Hi, I’m Jenn and I sold my first house at only 3 years old.
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#23. This is a picture of my Dad during our 1997 trip to Disney World in Florida. Fanny packs and mid-riff shirts, and nut-hugging shorts were Dad’s preferred ensemble.
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#24. My mom had me skip preschool to go get glamour shots with her. Think it was the right decision.
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#25. My daughter was having a tantrum, and hid her face under a pillow. The results were Divine!
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#26. My great-grandmother worked for a photography studio in the 80’s. She was watching us one day and decided to surprise my mother with professional photos of the three of us. This gem was one of the pictures. It’s safe to say that my mother never put this one in a photo frame and it’s the center of family laughter when we bring out the photo albums around the holidays. I love how my sisters look so cute in the corner of the photo while I am in a food coma floating in the sky.
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#27. My sister on her wedding day.
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#28. This photo was taken at a safari park in Oregon around 2000. As we walked into the park my sister saw a baby goat and picked it up while I was feeding one of the deer and the next thing I know I was bombarded by deer and goats. My parents snapped the photo of my cute sister without seeing me in the background.
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#29. “When my son hopped on the bed and his elbow nailed me right on my c-section incision.”
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#30. Our parents used to tell my only brother and me that we used to have another brother who turned into a mushroom from not taking a bath. Even added him to the family albums.
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#31. I show my boyfriend ONE picture from my childhood and suddenly reproducing with me is off the table.
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#32. My great-grandmother after wrapping her Skoda around a tree.
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#33. This is my son. That’s me next to him. Apparently, enchiladas make you tired.
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#34. My Mom’s bed hung from chains, and she had a mini bar for a headboard. 1972.
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#35. Me being an Uber Goth teenage posing next to tombstones unknowingly covering the ‘S’ in ‘Sweeney.’ Kind of ruined the mood of the photo!
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#36. My family went on a trip to Maine during the summer and decided to take family photos. Maybe it was very windy but everyone looks catalog perfect and then…there’s me.
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#37. This was my Christening, June 1971. I’m the baby obviously, my Godmother is holding me, my parents are next to her. Their hideous outfits aren’t the “awkward” part of this photo. In the background, my grandmother is pulling my sister’s hair while my brother is recovering from a smack! All of this right on the front steps of a church.
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#38. My dad hid a camera to find out why the cats kept sneaking into my old bedroom after I’d left for college…
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#39. My brother and I took a pony ride at the Whaling City Festival in the 80s and the pony ride operator had swagger.
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#40. My mom and dad in DC in the late 80s.
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#41. This is a photo of my daughter and her father riding the Tennessee Tornado roller coaster at Dollywood. When we saw the photo at the sales kiosk, we laughed so hard we just HAD to buy it!
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#42. Here’s my Mom and Dad in September 1970. This was always my favorite photo from their wedding because it’s just so cornball. You have to give credit to the photographer for the picture of my dad in the TV. This was years before Photoshop, so I’m not sure how the heck he pulled this trick off.
Source: awkwardfamilyphotos
Let’s be honest—no family is immune to the glorious disaster that is the group photo. Whether it’s Uncle Ron blinking mid-sneeze, someone’s dog stealing the spotlight, or a sibling feud captured forever, these Wholesomely Funny Family Photos remind us that the awkward moments are often the most cherished.
Now it’s your turn! Got a hilariously awful (but still lovable) family photo hiding in a drawer somewhere? Share your favorite awkward photo story in the comments, or tag a sibling who still swears that hairstyle “was cool at the time.” Let’s celebrate the awkward, the adorable, and the absolutely unforgettable.
Because when it comes to family, perfect is overrated—funny is forever.
